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Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates.
J Org Chem. 2012 Aug 03; 77(15):6600-7.JO

Abstract

The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang W
Institute of Chemical Biology, Henan University, Kaifeng, Henan, P. R. China, 475004.
Tan D
No affiliation info available
Li L
No affiliation info available
Han Z
No affiliation info available
Yan L
No affiliation info available
Huang KW
No affiliation info available
Tan CH
No affiliation info available
Jiang Z
No affiliation info available

MeSH

AlkylationAllyl CompoundsCarbonatesCinchona AlkaloidsMolecular Structure

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22816444

Citation

Yang, Wenguo, et al. "Direct Asymmetric Allylic Alkenylation of N-itaconimides With Morita-Baylis-Hillman Carbonates." The Journal of Organic Chemistry, vol. 77, no. 15, 2012, pp. 6600-7.
Yang W, Tan D, Li L, et al. Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates. J Org Chem. 2012;77(15):6600-7.
Yang, W., Tan, D., Li, L., Han, Z., Yan, L., Huang, K. W., Tan, C. H., & Jiang, Z. (2012). Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates. The Journal of Organic Chemistry, 77(15), 6600-7. https://doi.org/10.1021/jo3012539
Yang W, et al. Direct Asymmetric Allylic Alkenylation of N-itaconimides With Morita-Baylis-Hillman Carbonates. J Org Chem. 2012 Aug 3;77(15):6600-7. PubMed PMID: 22816444.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates. AU - Yang,Wenguo, AU - Tan,Davin, AU - Li,Lixin, AU - Han,Zhiqiang, AU - Yan,Lin, AU - Huang,Kuo-Wei, AU - Tan,Choon-Hong, AU - Jiang,Zhiyong, Y1 - 2012/07/26/ PY - 2012/7/24/entrez PY - 2012/7/24/pubmed PY - 2012/12/12/medline SP - 6600 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 15 N2 - The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22816444/Direct_asymmetric_allylic_alkenylation_of_N_itaconimides_with_Morita_Baylis_Hillman_carbonates_ L2 - https://doi.org/10.1021/jo3012539 DB - PRIME DP - Unbound Medicine ER -